Functionalization of hexa-peri-hexabenzocoronenes: Investigation of the substituent effects on a superbenzene

Ryuichi Yamaguchi, Satoru Ito, Byung Sun Lee, Satoru Hiroto, Dongho Kim, Hiroshi Shinokubo

Research output: Contribution to journalArticlepeer-review

31 Citations (Scopus)


We have demonstrated that the iridium-catalyzed direct borylation of hexa-peri-hexabenzocoronene (HBC) enables regioselective introduction of boryl groups to the para-, ortho-, and meta-substituted HBCs in high yields. The boryl groups have been transformed into various functionalities such as hydroxy, cyano, ethynyl, and amino groups. We have elucidated that the substituents significantly influence the photophysical properties of HBCs to enhance fluorescence quantum yields. DFT calculations revealed that the origin of the substituent effect is the lift in degeneracy in the frontier orbitals by an interaction with electron-donating and electron-withdrawing substituents at the para- and ortho-positions. The change in molecular orbitals results in an increase of the transition probability from the S0→S1 states. In addition, the two-photon absorption cross-section values of para-substituted HBCs are significantly larger than those of ortho- and meta-substituted HBCs.

Original languageEnglish
Pages (from-to)178-190
Number of pages13
JournalChemistry - An Asian Journal
Issue number1
Publication statusPublished - 2013 Jan

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Organic Chemistry


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